HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrabutylammonium Fluoride → (4R,6R)-6-([1S,2S,6S,8S,8aR]-2-{1,2,6,7,8,8a-Hexahydro-6-hydroxy-8-[2-(4-fluorophenoxy)-2-methylpropionyloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-hydroxy-2H-pyran-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | (4R,6R)-6-([1S,2S,6S,8S,8aR]-2-{1,2,6,7,8,8a-Hexahydro-6-t-butyldimethylsilyloxy-8-[2-(4-fluorophenoxy)-2-methylpropionyloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one | HCID 54026108 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (4R,6R)-6-([1S,2S,6S,8S,8aR]-2-{1,2,6,7,8,8a-Hexahydro-6-hydroxy-8-[2-(4-fluorophenoxy)-2-methylpropionyloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-hydroxy-2H-pyran-2-one | HCID 54259256 | 76.1% |
Reaction Steps
A procedure similar to that described in Example 2, above, was followed, but using 1.08 g of (4R,6R)-6-([1S,2S,6S,8S,8aR]-2-{1,2,6,7,8,8a-hexahydro-6-t-butyldimethylsilyloxy-8-[2-(4-fluorophenoxy)-2-methylpropionyloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Example 175, above] and 20.8 ml of a 1.0 molar solution of tetrabutylammonium fluoride in tetrahydrofuran, to give 565 mg of the title compound as white crystals, melting at between 142° and 145° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05491167 |
| Source dataset | uspto-grants-1996_02 |
| ORD ID | ord-f4b0af285e2447d6920c6e1e7bbee181 |
| Source note | uspto-grants-1996_02 |